One reaction used to produce these compounds has a modification that uses Bestmann's reagent, and which classically uses dimethyl diazomethyl phosphonate, named for Seyferth and Gilbert, while more common methods include the 
One reaction used to produce these compounds has a modification that uses Bestmann's reagent, and which classically uses dimethyl diazomethyl phosphonate, named for Seyferth and Gilbert, while more common methods include the Corey-Fuchs reaction. Terminal ones have a pKA around 25, and this functional group is hydrogenated by sodium metal in liquid ammonia into trans-alkenes. This functional group has a bond angle of 180 degrees because the carbons involved in it are sp-hybridized. For 10 points, name this functional group which has a carbon-carbon triple bond.
One reaction used to produce these compounds has a modification that uses Bestmann's reagent, and which classically uses dimethyl diazomethyl phosphonate, named for Seyferth and Gilbert, while more common methods include the Corey-Fuchs reaction.
{alkynes}